Reaktion #5341

Reaktionsgleichung

tetronic acid

triethylamine

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

6-[4-(hexyloxy)phenoxy]hexanoic acid

HCl

→

4-hydroxy-3-[6-(4-chlorophenoxy)-1-oxohexyl]-2(5H)-furanone

Ausbeute 43.0%

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted three times with ether
2. 2
   TrocknenThe combined organic layers are dried over MgSO4
3. 3
   Einengenconcentrated in vacuo
4. 4
   Sonstigegiving a yellow solid
5. 5
   Filtrationfiltering

Vorschrift

To a stirring solution of 554 mg (5.54 mmol) of tetronic acid in 20 mL of diemthylformamide is added 850 μL (6.09 mmol) of triethylamine and 220 mg (1.765 mmol) of 4-dimethylaminopyridine at 0° C. Next, 1.26 g (6.63 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 1.475 g (6.63 mmol) of 6-[4-(hexyloxy)phenoxy]hexanoic acid are added and the reaction mixture is stirred 2 days at room temperature. The reaction is acidified with 1.0N HCl and extracted three times with ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo giving a yellow solid. Pure material is obtained by trituration in ether, filtering to give 774 mg (43%) of 4-hydroxy-3-[6-(4-chlorophenoxy)-1-oxohexyl]-2(5H)-furanone.

Quelle